Hey there! We’re ContactMonkey 👋

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About the job - Manager, Customer Success - SMB

As the Manager of SMB, you will be the architect of our "Small and Medium Business" segment. Reporting directly to the Sr. Director of Customer Success, you will oversee a team of Onboarding Specialists, Junior and Intermediate CSMs. Your mission is to balance high-growth targets with operational efficiency, ensuring that our SMB customers receive a world-class experience through scalable, repeatable processes. You aren't just managing people; you’re building the machine that drives retention and expansion at scale.

Your impact

Team Leadership & Coaching

• Lead, mentor, and develop a team of Onboarding Specialists and CSMs, focusing on their professional growth and daily performance.
• Set clear KPIs for the team around GDR, NDR, and operational health.
• Manage the internal pipeline and training for new SMB CSMs as the team scales.

Operational Efficiency

• Build and refine "tech-touch" and "low-touch" workflows to prioritize retention and ensure no customer falls through the cracks.
• Implement automations and playbooks to reduce manual workload.
• Constantly evaluate the team’s BoB to ensure balanced workloads and maximum efficiency.

Growth & Retention Strategy

• Accountable for the entire SMB segment’s retention and expansion target
• Identify trends in SMB churn and develop proactive "save" playbooks to mitigate risk.
• Working with leadership to identify new expansion opportunities (upselling to new tier, longer term contracts, customer advocacy etc) to contribute to business growth and revenue generation
• Act as the "Voice of the SMB Customer" in cross-functional meetings with Product, Marketing, and Sales.

Reporting & Visibility

• Provide accurate weekly and monthly forecasts of renewals and growth within the SMB segment.
• Use existing tooling (SFDC, Pendo, Intel, Gong, etc.) to report on team productivity and customer health scores.
  
  

About you

• 3+ years of experience in Customer Success, with a proven track record of informal leadership (mentoring, leading projects, or SME status).
• You don't just solve a problem once; you build a process so the problem doesn't happen again.
• Ability to distill complex data into actionable insights for the Head of CS and SLT.
• You have a passion for "doing more with less" through automation and smart segmentation.
• You demonstrate a strong ability to think critically and solve problems independently. In this evolving leadership role, you’ll be resourceful and proactive, doing your own research and applying critical thinking before escalating issues.

How you can stand out

• You have a strong interest in ongoing learning and professional growth. Whether it’s through industry podcasts, books, or webinars, you refine your leadership style and share useful insights with the team, helping everyone develop together.
• You’re comfortable navigating change and leading your team through transitions, refining processes as we grow together.

What we bring to the table

🏥 100% employer-paid benefits + a Health Spending Account from day one

🌎 Work from anywhere in the world for up to 4 weeks

💰 Stock option plan—own a piece of our success

💲 RRSP Group Savings Plan to plan for your future

🏝 Generous vacation package to recharge and relax

📚 Personal development budget to fuel your growth

🧖 One personal day + two volunteering days to give back

🎂 Your Birthday off—celebrate on us!

🍎 Five health days per year to stay at your best

💼 Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks

Compensation & Work Details

The salary range for this role is $90,000 CAD- $120,000 CAD. Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.

We’re always happy to answer questions about compensation throughout the hiring process.

This is a net new position based out of our downtown Toronto office, at King and Spadina. Our team works on a hybrid schedule and is in the office 3x per week to promote collaboration.

Who We Are

Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.

Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.

We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:

• Ranked by the Globe & Mail as one of Canada’s fastest-growing companies
• Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years
• Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America
• Raised $55 million Series A financing in 2023

Diversity is our strength

At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.

AI Disclosure:

We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.